May's Pink Surprise
by jjscriptease
Summary: Ash's obsession with being the best pokémon trainer ever leaves May on the sidelines. He bumps into his archrival, Gary Oak, who just happens to be on the lookout for a worthy conquest…


**Disclaimer:** I do not own Pokémon and stand to gain no profit from this fic.

**A/N:** Rated M for a reason.

**May's Pink Surprise**

_j.j. scriptease_

Gary lounged in the deckchair beneath an umbrella, chewing gum, arms behind his head, fashionable shades on his brow, an air of cool about him, gifting all beach dwellers the sight of his toned abs. He pointed at a beautiful girl modelling along the shoreline. "That one."

Brock reclined beside him, also clad in nothing but beach shorts. He pointed at a girl in a blue bikini among the masses. "That one."

"Nice," said Gary. He pointed out a long-legged beauty sporting a one piece costume. "That one."

Brock nodded, impressed. He pointed at a woman baring a striking resemblance to Officer Jenny. "That one."

"Heh, just your type." Gary pointed towards a trio of girls in bikinis tossing a beach ball around.

"Which one?" asked Brock.

"All of them." Gary smirked. "At the same time."

"Bullshit."

"Would I lie to you?"

"Not even you're that good."

Gary let out a sarcastic laugh. "You realise you're talking to someone who spent all their trainer years stalked by a loyal band of cheerleaders, right? And in case you're wondering, I'd point all of them out if they were here too."

"Show off."

"Hey, you're the one who wanted to play this game."

"Yeah, well, it's not fun anymore."

Gary laughed. He appreciated Brock's envy. The wealth, fame, exceptional genes, and having a world renowned professor for a Grandfather, almost felt like cheating sometimes. What a lot of guys like Brock didn't realise though was how boring his life could be. Gary appreciated the art and softness of the female form as much as the next red-blooded guy, but at some point it all started to blend into a generic muddle of boobs, butts, and limbs. Even the most stunning girls made him go 'meh' the second they started grovelling. Their willingness to lie back and throw their legs apart zapped all the fun out of it. What good was a trophy if it was just handed over?

Gary felt a ping of regret reminiscing about the proverbial 'one that got away.' "Say Brock, what ever happened to that girl you used to travel with? You know, the redhead," he said, pretending not to remember her name.

"Uh, you mean Misty? She headed back to the Cerulean City a while back. I saw her every now and then but unfortunately we're not as close as we used to be." A disturbing thought occurred to Brock. "Don't tell me she's on your list too."

"Ha. I wish," said Gary, matter-of-factly. "She's fair game, right? You wouldn't have a problem, would you?"

"Me? No. Although, I should warn you. She only has eyes for Ash. At least back then."

"Figured as much. She had some serious legs though. Don't know what she ever saw in that dweeb." Gary smiled at a sad memory. "You know I even wrote a song for her?"

"Are you serious?"

He cleared his throat.

_"I wanna suck_

_Misty's breasts_

_Like no one ever has…_

_Ta da Dadaa~_

_To touch them is my real test_

_To shag her is my caaaaaaaause…_

_Ta da daa!_

_I will battle_

_With every man_

_To spread her far and wide…_

_I'll shag her till_

_She cannot stand_

_And makes me cum insiiiiiiiiiide!_

_Poke-a-hole!_

_ Gotta shag 'em all –"_

"That's terrible," said Brock, chuckling.

Gary cracked himself up.

"What's so funny?" asked a voice behind them.

They glanced over their shoulders, and sure enough, the boy who'd just graced their conversation stood there. Brock was ecstatic to reunite with a friend he hadn't seen in years. Gary and Ash were more like frenemies than companions, but he had to admit, seeing a familiar face stirred a little nostalgic sentiment. Teenage Ash looked like a ganglier version of the boy he remembered – except now he wore an even more ridiculous league cap. He and his Pikachu dressed in matching beach shorts. It might've been cute when he was ten, but it was plain dorky now, Gary thought.

"So you guys are like best friends now?" asked Ash.

"Let's just say we're bonding over shared interests," said Brock.

"Why don't you join us?" asked Gary, never passing up an opportunity to outshine Ash. "All you have to do is look around and tell us which of these sexy beach babes you've used your String Shot on."

Ash scratched his head, confused. "Why would I do that?"

Gary facepalmed. "I mean, who got your Weedle wet? Whose Jigglies have you Puffed? Who's stroked your Ekans?"

"Who's shined your Onix?" Brock tried one.

"Uh…" Ash shrugged. "I don't know what you guys are trying to say." Both Gary and Brock tumbled over their deckchairs, struck down by the unbelievable naivety. "Hey, are you guys making fun of me? I expected as much from you, Gary," said Ash. "How about it then? A pokémon battle! We'll see who has the last laugh then."

"You haven't changed one bit." Gary sighed. "No can do. I thought I already told you, I'm not a trainer any more. I'm a pokémon researcher."

"You're a chicken is what you are!" Ash and Pikachu mimicked flapping wings.

Gary waved them off. Ash's body might've grown but he was still ten inside.

"Anyway," said Brock. "What we were trying to ask is if you've scored with any of the wonderful ladies out here." He winked.

"Oh…" Ash rubbed the back of his sheepishly. "No, can't say I've ever done that." Gary smirked in the background. "But," Ash continued. "I do have a girlfriend now."

Gary snickered. "So you finally got around to asking your Pikachu out, huh?"

"Very funny, Gary," said Ash. "Actually, she's right over there."

Just as he pointed to the beach, her head broke through the water's surface, drenched tresses clinging to the sides of her face. Her eyes savoured the moment, awakening in slow, teasing increments, sapphire pearls that sparkled brighter than the ocean she emerged from. The angel smiled genially, but fiercely, shining against the backdrop of crashing waves and racing hearts. Her bosom burst out the depths, lifting water with a mighty ascent. The V-shaped bikini top allowed generous portions of her chest to bask in the sun as water rolled down the milky slopes and seeped through their valley. Her torso arched inwards at the hips, flaunting the curves of a woman, boasting the abs of an athlete. Droplets dribbled down her navel and meshed at the rim of her bikini bottoms. She strutted onto the shore with her hips parading slow seesaw motions, hypnotic as shapely legs climbed out of the ocean, inch by titillating inch. The brunette glimmered like a ruby amongst rocks on the coastline.

As Gary and Brock picked their jaws off the ground, Ash grabbed her attention with a wave. "May, over here! Come say hi to my friends."

She flashed pearly whites and jogged over. Gary was mesmerised by her wet, bouncing breasts glistening in the sun. He'd rarely seen naturals that size on a lean, fit girl. They were large, but not grotesque, with just the right amount of spring to make all the beach balls jealous.

Brock decided his hearing or vision was lying to him. "That's…May?" He looked again, unconvinced.

"I can't believe you haven't hit that yet," said Gary.

Ash flushed. "We're saving it for a special occasion!"

"Being with a girl like that…you'd think every occasion is special." Gary drifted for a second. As she drew closer, he and Brock scrambled out of their lazy stupor, spraying their breaths, straightening their hair and sitting positions.

"You remember Brock and Gary," said Ash.

"Brock!" May squealed. "It's been so long!" She pulled him into an embrace, one he was thrilled to be a part of, his pink face hidden over her shoulder. "And you're Gary? Have we met?"

The dashing pokémon researcher flinched. "You mean you don't remember me?" A girl forgetting him hadn't happened since like, well, ever. Granted, he failed to recall any previous encounter with her too; she must've looked totally different, he reasoned. "I still get a hug though, right?" He flashed his best smile and stretched out his arms.

"Er, let's start here." The bashful girl offered a handshake instead.

Now she was turning down his hugs too? What the hell was going on here?! Gary shook her hand all the same, not letting his disappointment show.

"You look really good, May," said Brock.

"Aw, thank you! I'm digging your new look too. The afro's definitely better than the spikes!"

"I don't know," said Gary. "Spikes aren't bad if you know how to work them." He flicked his own to emphasis the point.

"I guess," said May. "Know someone who does?"

Gary facefaulted. The cheek of this one! He'd be insulted if he didn't love it.

She tugged on Ash's arm. "Hey, why don't you come take a dip with me?"

"No point coming to the ocean if you're not going to get wet," said Ash. "Nice catching up with you guys. Well, nice catching up with you, Brock. We should grab a bite some time. Gary, smell ya later!"

The spiky-haired researcher panicked. "Ash! Wait!" The pokémon trainer whipped around, confused. "I changed my mind," said Gary. "I'll have that pokémon battle with you."

Ash practically leapt for joy. "Alright!" He pumped his fist. "We're going to be ready, aren't we, Pikachu?"

"Pika pi!"

"Heh. Good luck. You'll need it."

As Ash and his girlfriend walked to the shoreline hand in hand, Gary zoned in on the brunette's pert exterior. His heart was racing, his head spinning, his mind all over the place. Confusion, trepidation, excitement, all combusting in his veins at once. A tilted smirk crept onto his features.

Finally, a challenge.

…

May leaned against her fist, nodding off as she gazed at the lonesome picnic basket. The baguettes she'd worked so hard on were going to waste. Ash's insatiable desire to be the greatest pokémon trainer ever butted into her hopes for an intimate lunch. Still, it was unlike him not to work up an appetite all afternoon, especially with the energy he exerted coaching his little fighters. The imminent confrontation with that Gary guy was more than a pokémon battle to him. May grasped the sentiment, having had her own share of rival coordinators, but it was disconcerting when she couldn't even talk him into food. Every time she beseeched him, his response would be the same: Okay, in 5 minutes! Please give me 10 minutes. Just 2 minutes, I promise this time! Or so he said, an hour ago.

Her PokèNav plopped with a new message. Dawn was online, a good friend and fellow pokémon coordinator. They often swapped tales of their achievements in recent contests. But Dawn let on her smilie-obsessed excitement was owing to something else this time. Something special. May didn't even have to press for details before they flooded her screen. Her eyes grew twofold as she scanned the text; Dawn recounted how a mundane trip that started with her and Kenny going to the Poké Mart ended with her back against an aisle of Super Potions and her childhood friend up her skirt. She apologised if the story was too personal but May waved off her concerns. In fact, the brunette was invigorated with curiosity, pushing for more detail as she repositioned herself so Ash wouldn't glimpse their conversation if he happened to whip around. May had never wanted to criticise her friend but the infamous pink skirt screamed 'easy access' and it was only a matter of time until some boy tried to ease his way into it. Reading Dawn's encounter however aroused a cocktail of unexpected stirrings, least of all envy. She was deviously grateful the blue-haired coordinator spared no explicit detail.

Soon Dawn had to leave despite May begging her to stay. Understandably, there was no contest between instant-messaging her and hanging out with Kenny, especially after the most recent development in their companionship. May couldn't help imagine what those two would get up to next. She watched Ash, hard at work with his pokémon, and wondered how Dawn would feel about lending her that skirt. Would he even bat an eyelid though? When Ash delved into his pokémon trainer zone almost nothing could pull him out.

In spite of her frustrations, she hated playing the nagging girlfriend. Rather than get in the way, she put aside her own selfish needs for his attention, deciding to do something nice for her pokémon. The effort she put into lunch had gone unnoticed, but her lovely little companions hopped and soared at the prospect of her Pokéblock recipes. She rummaged through her bag for ingredients to make a treat she named _May's Pink Surprise_. Her inventory would be sufficient if not for a shortage of Pecha Berries. Luckily, the woods they'd stopped in were part of Route 104, sat in the backyard of Petalburg City, her hometown. She'd explored the area countless times with her father as a little girl, well enough to know Pecha Berry trees could be found in the vicinity. When she informed Ash of her planned excursion, the preoccupied trainer muttered back, showing little acknowledgement of a single word she said. She rolled her eyes and wondered if he'd even notice she was gone.

To the inattentive eye, all the trees looked the same, but May could name every one, distinguishing the scent, shape and colour of their leaves. As she delved deeper into the woods, the sight of Ash and his pokémon faded into the background. Soon she couldn't hear them at all. Pausing, she contemplated whether it'd be a good idea to leave Ash on his own; his sense of direction was terrible, and he might've panicked when he realised she wasn't there. On second thought, nah. She was over-worrying. She did that a lot these days, often forgetting he was a big boy now, more than capable of taking care of himself. Plus he had a gang of pokémon ready to defend him to the death should trouble arise. Reassured, she continued her expedition.

May collected Pecha Berries using the bottom of her shirt as a net. As she hummed along, a distant voice interrupted her tune.

_"Poke-a-hole you know!"_

It sounded like singing. The melody was familiar although the lyrics baffled her.

_"It's a whore filled we live in_

_With a whore nude girl to see_

_Got a bangable face_

_And some brand new tits to use_

_But you still gotta shag 'em all…_

_Grab the breasts that you can see_

_Poke-a-hole you know!"_

The song came from a boy leaning against a tree, his back facing her. She crept up and tapped his shoulder.

He stopped mid-song and whipped around, startled. His shock shocked _her_. She squealed. The Pecha Berries tumbled to the ground.

May clutched her heart, calmness settling in as she recognised his features. He stood a foot taller than her, slim, flaunting a blemish-free visage and sharp jaw. Tinted glasses posed on his brow, and big, spiky hair strutted against the laws of gravity. His open collar showed off the dazzling pendant around his neck. He looked like he spent more time than her in front of the mirror, daubing on some arrogance here and there, practicing the slanted grin married to his face.

"So we meet again," he said.

"You're…that guy from the beach, right?"

He fell over upside-down, smacked hard by her failure to remember his name, again. "Gary Oak. And you're Ash's girl."

May beamed. "That's right." She knelt down and began re-gathering the berries. He decided to help despite her claiming she was fine.

"What are all these for?" he asked, tilting a berry between his fingers.

"May's Pink Surprise," she said.

"What?"

"May's Pink Surprise. It's a recipe. My own," she chimed.

"Can I try some?"

"Ha! Sure. Although, I should probably warn you it's a Pokéblock recipe for pokémon."

"Figures." He shrugged. "You named a Pokéblock recipe after yourself?"

"Less talking, more picking up." She winked, a polite 'shut up'.

The pokémon researcher took a moment to research her body. Now that she had some clothes on, the outfit nudged at his memory, a vague recollection of seeing it before. Long, thick bangs dangled from the bandana swathed over her head, cradling her beautifully symmetrical features. Her red t-shirt was buttoned up to her neckline, covering her commendable chest, but not hiding it by any means; if anything, the tight-fit highlighted her perky mounds. Beneath a white micro-skirt, black spandex shorts clung to her toned thighs and colour-coordinated trainers completed her attire. Gary fought staring too long, afraid dribble may escape his lips without him realising it. He couldn't imagine she'd filled out the costume this well in the past, certain he'd have remembered her.

She expressed suspicion of his activities, asserting there were better places to practice one's singing than in the middle of a forest. He pointed upwards where at a Shieldon clutched around a branch like its life depended on it. Weird, how did a Shieldon wind up on Route 104? The lost pokémon was afraid of heights and refused to come down. Gary claimed his singing helped calm its nerves. Judging by the sample she heard, May was more inclined to believe his singing was the reason it stayed put; it would've explained how the Rock-type got up there in the first place too. Gary said he'd stumbled into it on his way through the woods. He asked if she could help him bring it down. The thought of doing anything for this stuck-up, self-obsessed show off didn't sit well with her, and probably wouldn't with Ash either, but she couldn't look away from the frightened pokémon without guilt pelting her conscious.

"Oh alright," said May, settling down the berries in a neat pile.

"Great." Gary smirked. "Here, I'll give you a boost." He interlocked his fingers and lowered the crude foothold.

Her hands pushed off his shoulders as he hoisted her up. Stifling a grunt, he elevated her reach towards the branch, supporting her weight with relative ease. Her fingers stretched to their limits but wiggled a few inches shy of the troubled pokémon. Damn, this would've been so much easier if she'd gotten to finish her batch of May's Pink Surprise. She needed extra height and asked if he was comfortable with her foot stepping on his shoulder. He was more than happy to agree. And she didn't know the half of it.

The pink-faced boy gawked at the sights above as his sordid scheme came to fruition. Her skin-tight shorts brought out her form even better than he'd imagined, highlighting her cameltoe in full definition, eclipsing the sun in all its luscious glory. As the rescuer concentrated on dismounting the pokémon, he concentrated on the curvature of her vulva, tempted to reach out and chomp on the succulent fruit, if only his neck was as long as a Girafarig's. He marvelled at the way the spandex crinkled in and around her plump folds with every slight movement. The visual tease distracted his stability, and before long, he was struggling to maintain their formation.

For all May knew, her weight was getting the better of him. Wobbling precariously, she urged him to stay strong just a little while longer. Almost there! Her hand grazed the branch, snapping it as the tower all came crashing down.

One yelp and one hard-landing later, she stirred only to find herself lying on top of the researcher.

Gary lay still as a board as he miraculously woke up in her bosom. The heavenly puffs pulled away despite his murmurs not to go, despite his willingness to suffocate a happy man. They both turned to see the gleeful pokémon scamper into the shrubbery, free. Overjoyed with their mutual success, they'd all but forgotten their precarious positioning.

May's face swooped over him with cheeks redder than a Pikachu's. She apologised for the drop and he apologised for dropping her, but neither hazarded to untangle from the stroppy predicament, frozen in shock and embarrassment. Their eyes engaged in a slow, pensive dance. Gary struggled to read her intentions. He normally waited for a cue. But with this girl, things didn't happen the way they normally did. Throwing tact out the window, he grabbed the back of her head and pulled her down onto his lips.

May was taken by surprise, groaning in discontent as his mouth smothered her complaints. His arms restricted her attempts to pull away and his lips closed any distance she achieved. Fuming, she was ready to call him every name in the book, but when her mouth opened, his tongue accepted the unwitting invitation. The slimy sensation was icky at first, his persistent organ slithering all over hers. Then she noted a tang of strawberry. She loved strawberries. The remnants of his chewing gum threw water on her rebuttal. Her mind slowly slumped into a dreamy haze. Soon it was _her_ tongue doing all the chasing. His hands moved away from the back of her head, giving her all the opportunity in the world to break free. She didn't notice. Or didn't care. His hands rolled over her shoulders and snuck down the small of her back. She was still in dreamland, bobbing for strawberries, when a crude squeeze claimed her right butt cheek, shocking her into full consciousness.

"You jerk!" She slapped him and backed away.

"Heh." Gary stood up, massaging the handprint on his cheek. "Can't say that happens to me often. Or ever."

She crossed her arms, unamused. "Who the hell do you think you are?"

"Gary Oak. Only everything you long for. Admit it. You were loving it."

"Shut up. You tricked me."

"Please. I only started the ignition, but you kept revving and revving, didn't you?"

She huffed, wishing she'd smacked him hard enough to dismember that smirk.

"What are you so pissed about?" asked Gary. "It was only a kiss. Not like you haven't done that before, right?" To his surprise, she turned away without reply. "What? Are you serious?" Gary laughed to himself. "I swear Ash is such a g-"

"Gentleman," she cut in. "He'd never try to pull what you did."

"Is that right?" He took it as a compliment. "Why are you still standing here?"

"What?"

"I mean, if you're so offended and disgusted, why haven't you run back to Ashy boy yet?" As he expected, she didn't have an answer, so he decided to provide one for her. "See, what I think…" He took a step closer to her. "Is you like being here. You like me looking at you." He took another step forward. She took a step back. "Coz unlike Ash, I appreciate an exquisite specimen when I see one." He eyed her from head to toe. The standoff continued to move, him approaching, her retreating. "You and I are alike, May. We want the same thing. And you know it."

May backed into an oak tree. Cornered. No place to run.

She denied his every word, outwardly at the least. He was just a creep. Albeit, not the worst looking creep, but a creep nonetheless. He had the air of someone accustomed to getting everything they wanted, an undeserving snob with the world at their feet. She was in a loving relationship with someone who made a difference to the world every other day. Light-years spanned between him and Ash. Sure, deficiencies crept into their relationship like any other, but under no circumstances would she downgrade to a self-centred jerk. Even as his tall, imposing charm closed the gap between them to an inch.

Gary leaned one arm against the tree, slightly above the shorter girl. Her body language might've fended off most but it would take more than crossed arms and a turned head to make him look the other way. He lowered his voice into her ear. "So, May. How was it? Your first kiss ever?" The feisty girl mumbled something he wouldn't ask her to repeat. He let her unsavoury remarks roll off his grin. As far as he could tell, he had her on the ropes. "C'mon, May. You can't even look me in the eye and tell me to go away can ya?" He practically dared her to.

May couldn't believe he had the gall. She wasn't about to fawn over his stupid, cocky, miserable, intoxicating smile. How many hints did she have to throw at him? Criticism kept bouncing off his impregnable shield of vanity. How annoying. She really wanted to hit him where it hurt. What better way than to trump his silly challenge? Looking into his eyes and telling him to get lost was hardly the impossible task he made it out to be. Yet, she found herself needing to prepare before taking the plunge. She inhaled subtly then looked up at his piercing orbs. The words caught in her throat before fumbling out feebly. He chuckled, unconvinced. Inching his body closer, he let his strawberry-scented chops hover at the tip of her nose, teasing as he asked her to try harder in a low, sensual purr. She cleared her throat, uncomfortable with his proximity, but determined nonetheless. Her flimsy eye contact betrayed weakness and Gary sought to pounce on it.

His lips dipped lower. Tantalizingly lower. May whipped her head to the side, keen on avoiding another blunder. However, offering her neck in the process threatened to be just as detrimental. His lips pecked her up and down. She stifled a gasp at the soft, wet touches. The tip of his tongue teased her flesh with light strokes. He painted a thin coat of saliva on the side of her neck, let the cool breeze sizzle upon it, then reinforced the sensation another swipe of his tongue. She grew into the rhythm despite groaning her discontent. Encouraged by her feeble resistance, his chops clamped on her nape and sucked the breath out her lungs, a shot of adrenaline to her heart.

The sounds of his suction met her exhalations. She'd never anticipated this reaction, granted she'd never had anyone test the sensitivity around that area. He cradled her throat with a gentle hand as his tongue indented her erogenous zone, his lips spreading farther, wider, covering more ground in their aggression, yearning to suck the skin of her bones. The tugging of her flesh tickled in ways that made her body giggle. Although she reminded herself this wasn't her boyfriend Ash, her sensory nerves refused to discriminate. She could tell her assaulter was addicted to her flavour. He was practically making out with her collarbone. She fretted against the graze of enamel. Paranoid he'd bite. But when he finally did, it lit her skin on fire, a scorching sensation stirring her loins ablaze.

His hot breath poured into her ear. "May, your body's so soft." His touch trailed down her arm. The tiny follicles lining her limb heightened from the electric charge in his fingertips. He groped her hip, inciting a groan, somewhere between disapproval and appreciation. He acted on the latter. His wandering touch roamed her flat abdomen, revelling at her physical fitness. The sideways rub brushed the underside of her bosom. Even the slightest graze screamed how immensely soft her assets were. Still, he needed to experience the full spectrum. He reached for her chest.

May was on the verge of retort when he recaptured her lips. The taste of his hot, cherry passion washed down her words. It was a soothing addiction, overwhelming her in deep, brash strokes. His smouldering presence filled her mouth, hands running down her arms, the soft friction rousing her hairs. No, thought May, breaking the lip lock. She glanced left and right, panic in her eyes. "We can't…what if someone –"

He steered her face back to his and planted hot lips on hers. "Yes, we can."

She'd be careless to believe that, but common sense made little sense in times like these. The kiss grew more frantic, heads tilting, lips absorbing one another. He squeezed her ass, moaning at its tautness. An illicit charge pumped through her veins as he groped her, patience plummeting. The purrs of his desperation were contagious. Some semblance of decency urged him to stop, albeit with muffled conviction, and fear of losing what wits she had left. His hunger was insatiable, targeting her nape and collarbone when her lips became unavailable. Her own hands were inspired to rummage around his biceps while his emphasis fell upon her thighs. He seemed hell-bent on testing her loyalty, and at this pace, she was failing wonderfully.

"Wait," she exhaled, but did nothing to stop him unbuttoning her shirt. Working his way down, he granted her light kisses, distracting her from her inhibitions. As the last button came undone, he threw her shirt open, exposing her undergarments to the breath of daylight. He stalled for a second, as if to appreciate the view, making her feel rather self-conscious. Not to mention irresponsible. Trainers walked down this route all the time, some of them as young as ten! That would be the death of her. She opted to cover up but he reached for her chest again.

His hand crammed into one of her cups and explored its squishy content. She blushed as he murmured satisfaction at her size and suppleness. He had coarse, inquisitive digits, rummaging in her bra like little critters, ticklish in new, scandalous ways. It was disparaging to think she and her boyfriend had never got this far. Ash was absorbed with his pokémon right now, none the wiser to his fiercest rival one-upping him in the cruellest way imaginable. If only he'd spared a moment to consider her needs. A selfish excuse, maybe, but how else could she justify wanting anything to do with Gary Oak? Ash was not without his compliments; he made her feel special, but Gary made her feel wanted.

She knew it had to stop at some point. The _when_ and _how_ eluded her. But somehow she'd cool from her hot and bothered state and disengage before the point of no return. She could do that, she told herself. This was nothing more than two agitated kids scratching each other's backs. Yeah, that's it. Just a little longer then she'd break it off, rush back to Ash and forget it ever happened. No harm done. Yeah…

Gary had other ideas.

The fondling had gone as far as he could take it, he decided, then lifted her breast out of its cup. She felt so exposed, and naked, even if it was only one teat; it was more than she'd revealed to any male. He handled her breast like someone who'd done it a hundred times. She wondered if he whispered in all the girls' ears how they owned the best set he'd ever touched. Genuine or not, his flattery rubbed her all the right ways, heightening her arousal, spurring the thought he wanted no one else like he wanted her in that moment. He massaged her tit round and round, pressing, nipping at the bountiful flesh. She felt her nipple harden between his long, stroking fingers. Was this really happening? Did she really want it to?

He lowered the side of his head onto her chest then she felt the tip of his tongue circle her areola. It was cold and wet, yet hot against her skin, fuelling the fire in her epicentre. He loved tormenting her. Her nipple was ripe and swollen, puffing out for attention, but the audacious tease traced around it again and again. Finally, his mouth enclosed her areola, trapping steamy breath over her breast before his tongue flicked into action. He started with faint strokes. Even the slightest of touches had her nipple exclaiming. The half-licks appeased her for seconds at a time. Not enough. She needed more. Her body offered a subtle thrust into his mouth. She knew he got the message when he caught her nipple between his teeth and sucked it hard, drawing a gasp of shock and ecstasy.

Her sensitive nub had never lived such pleasures and she struggled to hold it in as his chops licked and tugged on her breast. The sneaky researcher wasn't done there. In the midst of everything, a hand found its way beneath her skirt, with nothing but spandex as a final frontier, and a weak one at that. _No, not there_, were the words that sprung to mind, but never made it past her lips. She wanted to know what it was like to be touched there. Not-so-innocent curiosity perhaps, but God, if Ash wasn't going to do it, someone had to. Besides, she still believed she had it under control. She'd let him prod around the perimeter but not let so much as a toe through the door.

Gary showed every intention of exploiting the leeway granted to him. Without severing attention from her teat, he shoved his way between her thighs, practically cupping her crotch in one hand. May surveyed their surroundings again, as if this particular development warranted extra caution. The truth was she should've ended things a dozen steps before. She felt the heat of his palm beneath her shorts and she knew he felt hers too. Jeez, why was she letting this continue? He rubbed her fervently, further pronouncing her cameltoe. The width of his hand pushed her thighs further apart as he hungered for more. The friction of her shorts added spice to the sensations. Despite the formfitting spandex, his frantic bustling parted her nether lips ever so slightly, inducing a titbit of indecent pleasure. Too far.

"Hey…we have to stop," said May, half-words, half-pants.

"You really want me to?" he asked, rhetorically.

"Gary…"

He smirked. Now she knew his name.

He pulled his hand away.

She was surprised, maybe even disappointed, by his sudden retreat. She was more surprised when he plunged the same hand down her waistband. "Gary, don't!"

Her rebuttal came a second too late. Not that it would've stopped him. Not that she would've particularly cared. The feel of foreign fingers down there was surprisingly welcome. She supposed it was like any itch needing a good scratch and it often made little difference who the scratcher was. The body heat retained in her tights coupled with his vigorous fumbling formed a blistering storm of musk and moisture. She felt his digit draw a line over her slit, spreading her labia the breadth of a fingertip.

"Wow," Gary murmured. "Did you just use a Watergun attack or are you happy to see me?"

"S-stop it," she said, hiding her red face. "I have a boy…a boyfri-frie…"

"Heh, you want it bad don't you? It's not all that surprising, you know. 'Never' is a long time to go without any action." He moved his lips and fingers at the same time, teasing her slit up and down, until he suddenly stopped at her entrance. "Here, let me help you get up to speed." May whimpered as her walls were breached for the first time. He looked surprised by her reaction. "Jeez, that's only a third of my finger. This is going to be fun."

May thought he was exaggerating the numbers. She was astounded as more and more of his appendage materialised inside her. So long, she thought.

"So tight," he said, astounded in his own right. Never had the term 'snatch' been more appropriate. He worked her tightness through incremental rhythms, aided by her overflowing excitement. Just as well her shorts stayed on; they saved his shoes from an impromptu shower.

May was embarrassed by the squishy sounds he was pumping out of her. At this rate he'd drain all the fluid in her body. Spurt, spurt, spurt, and moans in between. Gosh, what if someone heard? It would be hard to explain why she was leaning against a tree with a boy's handprint churning in her shorts in the middle of a public route. And yet, the threat of an unknowing passer-by spotting them filled her with an anxiety that mixed with adrenaline, forming some fiery concoction of exhilaration. She couldn't say for sure what point her concern swayed from offending Ash to hoping no one would interrupt them. As he thickened the penetration with a second digit, she all but resigned herself to the inevitably of mortal sin. She was going to get fucked by her boyfriend's fiercest rival.

Or not, thought May, as she heard a voice in the distance. Fear struck her heart and she pushed Gary away, tidying up in a hurry.

"Would you relax?" He chuckled, holding up fingers drenched in May sauce. "That's not even in our direction."

She heard the voice moving along and realised he was right. "Doesn't matter. Still too risky. There's no time for this. Sorry." Wait, why was she apologising?

"No time?" He laughed off her excuses. "If time's your concern, you could've just said so."

No sooner had he spoke the words than had he been kneeling before her. May heard the sound of fabric ripping before she realised it was her shorts. Gary had fashioned himself a peephole at the front of her crotch. She blushed furiously, knowing his line of sight sat level with her exposed nether regions.

Gary gawked at glimmers of her pussy. It looked so cute and innocent, untouched, a staunch advocate of shaving, she was. He licked his chops. "Well, you did say I could have a taste of May's Pink Surprise."

"What? That's not what I mea- ah!"

Suddenly, May was looking down at the top of his head, face buried in her crotch. His proximity alarmed her. How could he be rubbing his nose down there? She hadn't been given notice to freshen up. Not only did he not care, he claimed she smelt incredible. As if to prove his point, he kissed her on the pussy lips. May had clutched his shoulders intending to push him away, but after a few licks, her hands clasped him in place. He grabbed her buttocks for leverage and practically French kissed her wet snatch. His fingers dissected her nether lips and his tongue glided along their inner linings, sending a tingle up her spine, and when he reached her aching clit, May cried out for all the heavens to hear.

He pulled away and warned her to shush. Yes, yes, she nodded hastily, anything to make him continue. And as his tongue re-acquainted itself with her clit, she held it all in, every curse word in the book, every Legendary pokémon believed to exist. She contained it all in strained groans while pleasure mounted on the back of her knees. In response, he swung one of her thighs over his shoulder, aiding her balance but also drawing closer to her sweet spot. May's eyelids drooped, making it harder and harder to stay vigilant of oncoming trainers, pink fog thickening the all around her. At that point she didn't care. Her feet were off the ground, her head past the clouds. All she felt was his tongue pushing in and out of her damp entrance. His tongue flicking at her nub. His tongue thrusting wave after wave through her body. All she heard was her lover slurping up every ounce of ecstasy gushing down his gullet. How she hadn't drowned him yet she'd never know. How she was still conscious for that matter. It felt like she was hanging on a thread, numb to everything except intense pleasure. It possessed her, forced her hips to gyrate, her muscles to tense, her claws to dig into his shoulders, her pussy to clamp his tongue tight. It screwed her eyes shut as rapture exploded from her core, rippled to her extremities and elicited a silent scream.

May looked down with a flushed expression dotted in sweat. He gazed into her hazy blue eyes and lapped up her cum. She tasted herself when he imposed another deep kiss. Although the orgasm had consumed her energy, his affectionate lips and vigorous tit massages dampened her cunt again in a matter of seconds. Her hands roamed beneath his shirt and his bulge grinded on her navel as they immersed into a full-blown make out session. Although May anticipated what was coming next, her heart fluttered when she felt him undoing his pants. If anyone would've predicted her first time was going to be up against a tree in the middle of Route 104 with her boyfriend's scumbag nemesis, she would've called them crazy, amongst other colourful expletives. But here they were. Ready or not. Right or wrong.

His pants dropped around his ankles.

She gasped as he scooped the back of her thighs and hoisted her off her feet.

Then she felt it. Big. Round. Probing at her entrance. Too big, she imagined, as it prodded blindly as if it didn't know the way in. Granted, with their hot and heavy bodies wedged together, neither of them had the vantage to make the consummation seamless. His heady dick slipped and slid over her juices, occasionally grazing her clit to blissful effect. It thrilled and frightened her. The longer he prolonged it, the more anxious she became, nervous someone might spot them, nervous she'd miss out on cheating.

"Do it," she muttered. "Now…"

Gary expressed shock for a second, then slithered into a grin. With one hand, he reached underneath her thigh and stretched his middle digit just long enough to find her saturated lips. He hooked one side with his fingertip and tugged it until the tip of his dick could peek into the entrance.

May exchanged eye contact with a Taillow flying overhead. In that brief glimpse, she saw guilt reflected in its eyes. The bird pokémon flew out of the picture, and a second later, May lost her virginity.

Despite his slow and meticulous efforts, she grimaced with every thrust, parting her further away from innocence. Her folds stretched with almost as much pain as pleasure. Two fingers couldn't have prepared her for the enormity to come. He pressed her back against the tree and kissed her throat, tasting the moans vibrating in her voice box. Between laboured breaths, he murmured shock and elation at her tightness. May would've complimented his size in return but pants and moans worked her mouth beyond coherence, her hungry cunt gobbling up more and more, salivating around his thickness. He was so damn big, granted, she didn't have anyone to compare him to. One thing was for sure though, Ash wouldn't have the balls to fuck her raw in the woods. The thrill magnified every sordid sensation perverting her. She never wanted her boyfriend's enemy to stop fucking her.

While May grew more accustomed to penetration, Gary grew less patient in his thrusting. Fingernails digging into her thighs, he ploughed through her ripped shorts at a furious pace, a battering ram on fire. Each thrust knocked her ass against the tree, dragging her back up its bark. The discomfort was a small price to pay for the pleasure being pumped into her. It alarmed how fast she'd gone from sexually frustrated to taking more dick than she could handle. He immersed himself to the hilt of his cock, pulled back, then did it again, and again, and again, a squelch and a cry each time. It was as if he was trying to shove his entire body through her tiny gash. She felt every last bit of him and then some. His pubic hair patted her bare labia, adding a prickly kick to every thrust. He yanked down the other half of the bra to free her neglected breast, if just to watch them both bounce in tandem. Pressing his body against hers, he squished her chest as their moan-full mouths reunited. The sloppy kiss was rocky from the turbulence of his thrusting. Drenched in each other's sweat and saliva, they fucked like wild pokémon in heat. Her gash sprinkled lust all over his shins and the roots of the tree. Several pumps and squelches later, May broke the kiss to express euphoria at a second orgasm.

Gary warned her he was close to his own and wanted to sprint to the finish. The ricochet of wet smacks doubled in speed and intensity, the ripples bobbing her head up and down, dishevelling her bandana. She wrapped her arms around his shoulders, weeping in ecstasy as he climbed within touching distance of her cervix, filling her gash to the brim repeatedly. Then, all too abruptly, her thighs slipped out of his sweaty grasps. May touched down, feeling like she'd come off a rollercoaster, a little weary and off balance. She slumped to the bottom of the tree but barely had a moment to catch her breath when Gary aimed his cock at her face. She flinched as a hot spurt smacked her between the eyes. Grunting, he aimed more bursts at her lips and chest. May was out of it, heaving as he bathed her in a white-hot shower, his essence sliding down the slopes of her breasts.

Gary did up his trousers with a smirk. "Always one step ahead of Ash," he said, admiring his work. "Some things never change."

"Wait." May raised her hand before he fled the scene. "You can't…you can't tell Ash."

Gary was taken aback. After the spin he'd just put her through, all she could say was 'don't tell Ash'? "Whatever." He waved a hand whilst walking away. "Till the next time. Try not to dream about me too much."

As May stooped with her body dripping another guy's cum, a sudden wave of regret crashed over her, her senses rapidly returning. "Ash…" She tidied up herself the best she could, pulling down the skirt to conceal her ripped tights. She rushed back despite the soreness of each step.

…

May returned to camp to find Ash and his pokémon had ransacked the picnic baskets. Under normal circumstances, she would've been angered. All she could do after her jaunt was give a bittersweet smile.

"Hey, May. Where did you go?" asked Ash with a mouth full of sandwich.

"Oh…just to get some Pecha Berries."

"Oh yeah. Glad you're back. We were starting to worry about you."

"Pika!" Pikachu climbed onto her shoulder. The rodent pokémon offered a hug when he noticed odd imprints on her neck. "Pika pi?"

May hid the hickey under her collar hurriedly. "Oh that? That's nothing. Just a scratch." She chuckled sheepishly, holding down the hem of her skirt.

Ash ignored her awkwardness. "So where are they?"

"Where's what?"

"The Pecha Berries!"

May smacked her forehead. "Oh, that's right. I, uh, kind of forgot them."

"Too bad." Ash sank. "My pokémon were really looking forward to May's Pink Surprise. Just the right thing to get them jacked up for tomorrow's battle!"

"I'm so sorry, Ash. I'll see if I can make something just as good, okay?"

The day went on as normal. For Ash and his pokémon anyway. Eating, training, eating some more, training for dessert.

Meanwhile, May harboured the turmoil of her deceit. Even as the sun went down and the moon came up, the terrible incident replayed through her consciousness. It kept her up, lying in her sleeping bag, gazing at the stars while Ash and Pikachu snored the night away. She couldn't believe she'd discarded her virginity in such a sleazy way. Thankfully, she had spare biker shorts to replace the damned pair she tossed away, but getting rid of the memory wasn't that simple. The more she thought about it, the more vivid the imagery, the sin, the passion. Before she knew what was she doing, her hand slipped through her pyjama bottoms and her imagination ran wild into the night.

…

Gary looked at the stars through his window, patting the Shieldon sitting on the sill. He owed all his gratitude to its Oscar-winning, damsel-in-distress performance. If it wasn't for that, he might've had a harder time pinning down his target. And what a target it was. When he closed his eyes, he could still feel her soft, tight body pressed against that tree, still see her magnificent bosom bouncing at his behest, still hear her hot moans pouring down his ear as he drove Ash's girl to her climax. Pity for the time constraint. He would've loved to give her plenty more. Gary chuckled, just imagining the look on Brock's face when he found out.

For the first night in a while, Gary didn't dream about Misty.

…

"We won, we won!" Ash hurled Pikachu in the air. Trainer and pokémon overcome with laughter and triumph.

Gary grunted. "Lucky break. Golem, return." Defeated, the rock-type was zapped up into its pokéball. The only thing more annoying than Ash Ketchum was losing to Ash Ketchum in a pokémon battle. Watching his over-the-top celebration grated the nerves. May's rejoice seemed somewhat subdued, not that the overjoyed trainer noticed. She shied away whenever Gary glanced in her direction. Although he'd never admit it, Gary had been hoping to impress her by destroying her boyfriend on the battlefield, as if he hadn't done enough already.

"It's skill, Gary. Skill," said Ash.

"Pika-chu!" The rodent agreed.

"Whatever," said Gary. "You make me nauseous."

Ash stuck his tongue out. "Sore loser. We're outta here. Till the next time you want to lose to me." He and May set off.

"Hold it. Where to?"

"Uh, I don't see why you care but since Petalburg City is around the corner, we've decided to drop by and visit May's folks."

"Hm, interesting." Gary tapped his chin. "I'm headed the same way," he decided.

"Uh? Really?"

"Yeah. I've got a paper on the habitats of Shieldon to present to Professor Birch." He jumped between Ash and May, wrapping his arms around their shoulders. "It's your lucky day. You get to travel with me."

"Yeah…real lucky," Ash droned. "Just try to stay out of my way, okay?"

"Trust me, Ash," said Gary as they began to walk. He snuck a pinch of May's ass. "That's going to be the least of your worries."

She glanced at him in the corner of her eye. Her lips twitched ever so slightly.

On the contrary, Ash, thought Gary. _He_ won.


End file.
